Between the Devil and the Bourbon Bottle
by FoulkseyDarkRose
Summary: The Winchesters go to Chicago to search for a mysterious Rebekah about a possible Demon-Vampire army and they cross paths with Elena and Damon in the search for Stefan, who has become Klaus' little bitch. After a series of unlikely events, the two pairs relucantly join forces to figure out what the hell is going on. ElenaxEveryoneButSam. Katherine, Elijah, Rebekah, Klaus star.
1. Chapter 1

**Between the Devil and the Bourbon Bottle**

**Chapter 1 - Tell Me All, Or The Toe Gets It. **

**Dean's POV**

* * *

"The moronic, damn, good for nothing ass hole!" Sam Winchester mumbled in his sleep, which Dean found a bit weird, even for their family. Fighting demons and ghosts? Check. Shouting at random people in our dreams? Not so much. Anyway, Sam was a heavy sleeper and who could blame him. Dean snuck sleeping pills into his cheese burger dinner before they went to bed. He couldn't fight nature; especially when it has a little helping hand from drugs. Dean knew many people would say that was immoral off him but at the end of the day the little guy needed protection from the horrors of their past.

That's why it struck Dean as wrong when he glanced at his little bitch of a brother writhing in fear and rumpling his sheets all over the damn motel room. _Just more of his messes for me to pick up, _the elder brother thought dryly to himself before rolling over to face away from his weird brother. His dad had drilled into him the impulse to protect Sammy boy from anything that goes bump in the night. Excluding women, Dean didn't want to stop that. In fact he needed to encourage it. Sammy was still mooning over his murdered girlfriend which was definitely putting a damper on the whole brother bonding road trip style thing that happened in the movies.

Dean didn't listen to everything his father had told him unlike what Sam thought. When living in a hunters life with John Winchester as your father you learn to take somethings he says with a pitch of demon-repellant salt. The total money ball recently was the promise that he would be back in a few days. _Where are you Dad?_ Dean thought to a random space before his eyes, which after focusing in the darkness of the night, Dean saw the face of an alarm clock.

Sammy moaned again. _Jeez what does it take to get some sleep around here? A tooth? _he thought. Not that Dean had ever lost a tooth before - he'd had several close calls a few times there when fist fighting with damn demons and witches. The witches liked to take teeth for their weird sexual-evil hybrid of rituals.

Great. He definitely wasn't getting any sleep now. Dean decidedly sat up and gingerly placed his feet on the dirty floor of the motel. Something sticky stuck to the ball of his toes and he nearly shrieked. Anything wet, unidentified and unexpected utterly freaked him out. _Except ma women,_ he thought to himself as he tiptoed to the bathroom that was opposite Sammy's bed. Dean made it carefully to the end of his bed, doubling over slightly to look out the window to his right. His baby was out there waiting for him, longing to feel her roundness and power was making Dean pout involuntarily. He paused mid-step, his eyes coming into contact with her - his beautiful '67 Chevy Impala. The Metallicar with all the added extras: the cassette player, the reclining seats, the sleek black finish, her V8 327 4-barrel engine, 275 horse power and her son-of-a-bitch arson and weaponary compartment in the truck.

He was grinning at what a lucky Impala she was, his little CAZ 2Y5 or he secretly called her 'Caz' for short, to have such a good-looking owner when it happened.

Sam started screaming in a pain that was worse than anything Dean had sure never experienced. He stepped quickly over to Sammy, using the broken lines of light which illuminated only certain parts of the room as a guide to not fall over Sammy's... Dean's toe, the one with the sticky stuff on it, somehow got slammed into the corner of Sam's research bag full of heavy, ancient books made with what could have been anything from rocks to metal to knives considering the shooting lightning bolts flying through the toe.

"Fuc-" He began to shout but as soon as he did, he lost balance and fell onto Sammy's bed which jolted the younger brother awake immediately. Dean was the one to writhe in pain now - this was the guy who had survived gun wounds, knife stabs, bites, sacrifices. It was like going to a diner and ordering strawberry pie when there's the mother of all apple pies on a two-for-one offer - just plain stupid.

"Dean? What the hell man?" Sam's quiet and creaky voice came from below his writhing body. _Right. _The brothers adjusted themselves and Sam went to sit on Dean's previously occupied bed onto to sit on a bra. Impatient, Sam threw the bra from Dean's escapades earlier that might straight at his elder brother's face. No that Dean minded, he kinda liked the girl it belonged to. _She was a fine one, _he tried to distract himself from the pain which was causing his face to scrunch up like when he tried to think of a girl's name the morning after, _she did this thing with her tounge.._

_"_DEAN." Sammy yelled, using his middle finger and thumb to squeeze the bridge of his nose. God, he looked like their father when he did that. If only daddy was there to see his freak show of sons who can't even talk to each other yet alone sleep in the same room without annoying each other. But that didn't matter, the fricking pain in his toe wasn't going away.

"I stumbled my two on your Chewbacca of a rucksack you bitch!" Dean

"Jerk," Sam replied with a sleepy smile before continuing, "I think there's a job for us, man."

"Whatever. I wouldn't care if _Dad_ walked in right now - my damn toe would still be like your sex life!"

"My sex life?" The smirk on his younger brother's face vanished immediately at the insult that he didn't really understand - Dean could see evidence of a bad night's sleep on Sammy's skin already. Dark circles, wrinkles, old lady moustaches... God his vision was searing up now too.

"Yes - I can't feel it so it isn't there."

"Oh ahaha. Can I tell you about my dream or not?" Sam stood up, proving just how not little he was, and walked over to Dean's enemy. That damn book bag. He pulled out Dad's journal and flicked through to the page of Dad's theories. Sam looked worried and handed a calmer Dean the journal.

It read:

**_Chicago: Demon and Vampire town? - see Rebekah M. She knows something._**

"Thanks, Sammy, that really makes me feel better," Dean rolled his eyes and massaged his cooling down toe. It wasn't on fire anymore so he could actually concentrate.

"Don't you see? Dad always wrote locations in coördinates. This is just written. Must be -"

The elder brother interrupted, "- A pretty big ass-slapping case. It says demon and vampire: so like a interbreeding sex maniac making babies?" Sam nodded in a solemn way. "How did you know to find that dude?"

"These premonitions - I don't like them Dean. So you don't have to get so patronising. All I saw was that page in Dad's journal in the hands of a blonde."

Dean perked up and looked more alive. "Was she hot?"

"Her name was probably Rebekah." Same teased his shallow elder brother meanly. Was it so bad that Dean could admire an attractive woman? It's not like he walks around f-ing every girl he sees. He has standards, just like everyone else. It just so happens that a smokin' girl always needs saving from the supernatural. Swoop in, save girl, get girl, move on. Dean smiled, _my life is friggin awesome. _

_"Answer the question Sammy boy or I'll tell everyone about the ruler you keep by your bed for when you-"_

"Okay, okay," Sam held up his palms in a surrendering motion, "She was very hot man."

"Tell sugar to not worry," Dean jumped up and ran into the bathroom. his toe forgotten, "Six inches is on his way!" He cried from the bathroom where he turned on the shower. He could hear Sammy packing, looking through his precious books that Dean had learnt long ago where not book porn. Sadly. "Oh, Windy City... here come the Winchesters!" He sang into the shower head.

* * *

**A/N: What do you think? Sorry I'm so sucky at writing but this story line popped into my head so.. viola! Next up.. Damon and Elena on the road.**

**-FoulkseyDarkRose**


	2. Chapter 2

**Damon's POV**

* * *

"...and drag you to the Devil. Na na naa na naa!"

"Damon, can you please shut up!"shouted the agitated brunette curled up in the passenger seat next to him. Her eyes were even more puffy and red than when they had left Mystic Falls, Virginia that afternoon. God, packing had been a nightmare. As soon as Andie Starr - Damon's compelled news reporter girlfriend - had told him about a string of murders happening in a path to Chicago, Elena had whirled around Stefan's room packing. She had stayed there ever since Klaus made her boyfriend leave home. She was stronger, yet broken. Damn love, it always got in the way. Stefan left to save him, to get Klaus to give his blood to save Damon from death.

Elena settled back into a sitting position and struggled to turn his radio down, nearly pulling the knob from its socket. She couldn't see past the never-ending tears in her eyes. Damon was willing to guess that she hadn't slept since Steffy left, but that was no reason to take it out on his radio volume knob.

"Whoa, _Sleeping Beauty_, what's gotten up your skirt tonight?"Damon remarked as he pulled the car into the outside lane to overtake some crappy french car. People these days just had no style. His 1967 Chevy Camaro was the best car around; smooth, ice blue and sleek. He was sure that any honourable car buff would agree with him whole heartedly by saying that _his_ car was probably the best Chevy. No wonder all he could think about was his car: Elena was being such a bore and the highway they were travelling on was seemingly long. And dark. There were few street lamps on this road which was stupid considering it was one of the major highways in Ohio. The occasional sign flew past the window, the odd car

"Damon," He saw Elena frown at him from the corner of his eye, "we need a plan."

"For what?"

"To save Stefan!"

An uncontrollable feeling of annoyance swept through Damon's bones. He had heard nothing but Stefan this, Stefan that... Stefan. Stefan. Stefan; it was always Stefan. His little bro sure knew how to hog these doppelgängers' brains. _Undeniable love_ and all that shit. Damon wasn't like that. He loved playing, laughter and happiness. Passion. Isn't that what all girls wanted? Apparently Elena wanted to settle for Stefan's cute, sweet and boring love.

"Elena, you know we have _nooo_ idea where the hell little bro' and vampire-doggy have run off to," He smirked at his own awesome humour, Damon was the nickname master. Among other things. His smile soon faded when he remembered the seriousness of what was happening, "We can't make a plan until we know what we're getting into."

His brother's girl was silent. It wasn't the type of silence Damon usually got with women - they weren't kissing nor passed out from a night of extreme dancing and drinking. She was above that. They had kissed once, back when Damon was..dying from a damn werewolf bite given to him out of the kindness of Tyler Lockwood's heart. She had whispered to him that, _"I like you how you are now,_" and kissed him farewell. The kiss said it all, and over the years Damon had more than his fair share of kissing varieties. He could tell that Elena Gilbert loved him. She just didn't know it yet.

But there was one thing they both knew - even Stefan knew it too. Damon loved Elena. She had been the one to reach out to him when Katherine betrayed him, when she had avoided him for 145 years of his valiant searching. Heck, Elena had even said she was sorry about _both_ brothers loosing Katherine in the fire... way before she knew about vampirism. She was a good soul. Her naturally tanned olive skin, her light shine and glowing aura, her flowing long chocolate hair that lit up with red when she stood in the sun. The way her chin came out in times of stubbornness. He loved her and by God it got annoying sometimes. She gave a gentle yawn that made his insides swell up - something he hadn't experienced since Katherine Pierce herself. Before he found out she was an evil slut vampire.

"Maybe we should stop at a motel. Ric mentioned a good place not far from here -"

"No. Damon, just keep driving." Elena ordered him in a monotone voice. Her eyes locked straight ahead, into the darkness. He nodded and felt his eyebrows furrow.

Some kind of modern-day pathetic excuse for music started playing from Elena's feet. Damon looked across at her only to find that she, too, was frowning.

"Expecting a call?"

"No, but that's not the problem," Elena audibly swallowed, "it's Stefan's ringtone."

The tempo rose higher and higher. Moaning voices harmoniously joined the beat, the volume getting louder as she took the HTC out of her leather bag. Of course Steffy would call her just as we hit the road. He knew his murder rampages would be in the news, that Damon would see through the cover-ups and lies, and his fan club would come running in on white steeds to save the day.

"Give me the phone, Elena." He wanted to hear his brother's voice.

"But -"

"Give. It." Damon snatched it out of her hand, holding the car in a steady pace with the other, ignoring her protests. He held the phone up to his ear and accepted the call.

"What's he saying?"asked Elena, the desperation far too clear in her voice. Damon shook his head and she shut up again. The other line was noisy. A bar or someplace. Music. Laughter. The old, fun Stefan's kind of place.

"Stop looking for me."Came his little brother's plea. It was almost whispered as well as hurried. Glass shattered in the background and Damon heard thuds and shouts over the loud music. A woman's voice in the background called for Stefan to come over and help clear out the 'newbies'. Stefan's breathing turned from the phone and the sounds became muffled. He had covered the microphone but Damon heard as Stefan replied, "Okay, Gloria... oh _shit_."

The phone rang dead as the call ended. Damon smiled at Elena as they crossed the border into Indiana. He handed the mobile back and paid better attention to the road.

"Why are you smiling? What did he tell you? Damon TELL ME."she demanded forcefully.

"Little bro told me where they are. _Exactly _where they are."


	3. Chapter 3

Chapter Three

**Dean's POV**

Sammy's headaches were getting worse; no amount of cheap liquor-store beer and aspirin was helping. The pain had reached even beyond that, or so the tumultuous breathing from shotgun altered Dean. His little brother had slumped back to sleep as soon as the Impala had hit the interstate. Now, feeling more alone than ever before, Dean drove and drove... trying not to think too deeply into anything. He focused on the case ahead, if it was even a case. _Sir_- no, Dean scolded himself. It had been years since he had called his father 'sir' like the good little solider he was. No,_ Dad_ always wrote cases in co-ordinates. It was his thing, like Sam's thing was farting and Dean's was drinking.

Rebecca. The name was common and yet he felt like it was important. What did this girl know? What was going on in Chicago? Too much was unknown; Dean was even thinking that maybe they should not go at all. His hands twitched on the steering wheel. Intake of breath. Rebecca Mikaelson. Not that wasn't very common – in fact it would make a good last name for his next batch of IDs – there was a sudden rustle to his right.

"Dean." Sam's voice came out of the dark followed by several groans. It freaked Dean to know that Sammy was all grown up now, sometimes it unnerved him. He still could hear the annoying, know-it-all high-pitched squeal of the eleven year old Sammy. An ache formed somewhere near his chest. Boy, had he matured so much since then. Well, Dean admitted, not matured; just seen far too much death. But if there was anything Dean knew about his now-old younger brother, it was when he needed a pee stop. Dean gave a dry chuckle and took one hand off the wheel to punch his brother in the shoulder.

"Sure thing, next stop isn't for a while though. Unless..." He reached his free hand behind the his driving seat. There was a bunch of old take-out wrappers, a few frosty guns, rattling loose bullets and.. there it was! Dean gave triumphant smile as he revealed an empty beer bottle, head tilted towards Sammy and eyes wide in innocence. His brother now had a furrowed brow and tight lips. "Oh, Samantha, please wipe that dirty diaper face away. Y-you have a wet diaper for once, instead." He chucked the bottle onto Sam's lap and burst out laughing.

"Just stop soon." Sam mumbled as he stubbornly spun the window handle. Clean air seeped into the Impala and played with Sam's mop head of a hair cut. Dean would have to cut that for him soon or it may get out of control and make him look ridiculous. The younger brother held the bottle between his pointer finger and thumb with a disgusted look on his face. He sat there, just glaring at the bottle. Dean made a grab for it and threw it out the window into the roadside. "Hey!" Sam protested as the bottle could be heard shattering on the side of the road behind them.

"What? You were looking like you were thinking about making out with it!"

"You're disgusting."

"Bitch."

"Jerk." Dean smirked.

They rode in silence for a little while longer. Listening. Dean appreciated these small moments. A hunter life for most meant no family, no friends, nothing; he and Sammy were lucky that they had each other. They both knew that. But sure as hell did it bring a lot of trouble. An Achilles' ankle, or something. Like this car, his Baby. If anything were to happen to them, he would give anything to get them back. Absolutely anything – the Heavenly sky's the limit. Light played against the black sleek hood of the Impala as dawn broke into the darkness. It shone like miniature stars, creating their own personal night sky. The little things. Sammy was watching it too, Dean saw out of the corner of his eye. The fresh light lit his kid brother was a soft glow; Sam's face was an image of calm, which was a rare moment. They had been driving for hours before either one of them spoke.

"So this Rebecca girl," Dean coughed out. His throat had dried over from being awed at she hot?"

"Jesus, Dean, I don't know. For all we know, she could be dangerous so don't-"

"Don't what?" Dean opened his mouth wide in offence although he knew too well that he was rather well-adjusted in the bedroom department. "Don't get some of what you ain't?" Sam scowled at Dean and turned towards the open car window. The morning was still brewing but the air was gaining heat.

"Anyway.."

"- oh, change the subject, how _original_-"

".. I think we need to do some more research into the area. Look for the usual, you know. Dead people." Sam shuffled around awkwardly, reaching into his jeans pocket. He pulled out his phone and stared typing some nerd-boy crap as usual.

"You do that, _Big Boy._" Sammy looked up from the phone, face harshly lit up by the blue light of the device, and glared sourly at Dean – who laughed. "We're nearly at the border, I - er – may have ridden too fast through Iowa." Dean checked the Impala's fuel gauge. Low, dammit. The pretty girl was lucky she was worth all of her cost.

"Um, okay."

"Nice talking to you, too, little bro." Dean returned to watching the road. It was eerily empty, practically unheard of for the Iowa-Illinois area. Weird, but not weird enough for them. He still doubted there was anything here. After all, they were trusting the brain of a home run away who kills monsters for an unpaid living. Yeah, exactly. Unreliable. Not that Dean didn't trust Sammy, he did, kind of, it was more to do with how supernatural he was becoming; a constant worry that Sam would be the next case to gank.

"I hacked the local police network -"

"You can do that on phones? Seriously?"

"Shut up, remember who you're talking to. So get this. There is no Rebecca or Rebekah or Beca Mikaelson on file. She's never existed, ever. No record of her."

"You don't think she is the case do you?"

"Yup."

"Well crap, the pretty ones always are the scariest." Dean sighed. This life could suck sometimes. "So.. you still want to stop for your appointment with Pee-pee?"

"Just drive." Sam gruffed back, shrugging back into the leather seats of the Impala like someone would on a couch. One day, Dean told himself, they would have their own couch. Their own home.

But for now, they had a supernatural nest to kill.

* * *

**A/N: Sorry it's been so long guys! I promise the 'teams' will meet soon and we will discover just how their paths will collide!**

**-FoulkseyDarkRose**


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